With spring weather warming up more consistently and the lakefront thawing into lovely aquamarine waves, May is a favorite time to explore Chicago before the large summer tourist crowds arrive. Consider these free or low-cost activities for your Chicago May adventures. Besides the essential … [Read more...] about Things To Do In Chicago in May
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Chicago Memorial Day Parade
The annual Chicago Memorial Day Parade and Wreath Laying Ceremony honors all men and women who made the ultimate sacrifice in defense of our country. This year's parade is scheduled for May 23, 2026. Head to Daley Plaza in the Chicago Loop to witness the moving Wreath Laying … [Read more...] about Chicago Memorial Day Parade
Belmont-Sheffield Music Fest
For many neighborhood festival fans, the Summer fest season officially kicks off with the cover band glory of the Belmont-Sheffield Music Festival, set for May 22-24, 2026. The 40th annual celebration of community and local musicians draws enthusiastic crowds to the streets near the … [Read more...] about Belmont-Sheffield Music Fest
Chicago Mayfest in Lincoln Park
Beer, food and cover bands are the hallmarks of the city's first festival of the summer, Chicago Mayfest. This year's 29th annual edition continues the tradition from May 15-17, 2026, in the Lincoln Park neighborhood. This year's fest will kick off at Armitage and Sheffield and … [Read more...] about Chicago Mayfest in Lincoln Park
Early Bird Chicago Boat Cruises for $20
It's that time of year! The season to enjoy Chicago views of gorgeous Lake Michigan has officially arrived and there's no better way to take in all the watery beauty than with a boat cruise. Chicago Party Boat is offering discounted Friday Night Skyline Cruises every Friday in May, May 1- 29, … [Read more...] about Early Bird Chicago Boat Cruises for $20
Sor Juana Festival Events
The annual Sor Juana Festival honors the historic Mexican writer, feminist and nun, Sor Juana Inés de la Cruz, with a dynamic line-up of artists, writers, filmmakers and singers at the National Museum of Mexican Art through April 29, 2026. Check out some of the exciting free … [Read more...] about Sor Juana Festival Events
Celebrate Spring with a Bonfire at Andersonville’s Valborg
Join the Swedish tradition of welcoming spring and banishing winter with a roaring bonfire, music, poetry, food and dance at the second annual Valborg in the Andersonville neighborhood on April 30, 2026. Sit around the bonfire and toss the worries you've written down into the flames to kick … [Read more...] about Celebrate Spring with a Bonfire at Andersonville’s Valborg
Free World Music Wednesday Concerts
The new season for World Music Wednesday has been announced! Every Wednesday, through June 24, 2026, at 8:00 pm, the Old Town School of Folk Music will host a free concert series, World Music Wednesdays, featuring musicians from all around the world. Culture and countries represented … [Read more...] about Free World Music Wednesday Concerts
Discount Tickets for Saturday Night at the Zoo
Experience the sights and sounds of the zoo after dark, visiting animals and sipping cocktails at this adults-only evening event, Saturday Night at Lincoln Park Zoo on May 2, 2026. Stroll through the grounds of Lincoln Park Zoo at night and enjoy special after-hours viewing of the … [Read more...] about Discount Tickets for Saturday Night at the Zoo
Art on the Mart
Stroll through the Riverwalk for views of one of the world's largest digital art platforms. ART on THE MART displays contemporary art projections across the 2.5-acre facade of THE MART. The spring show features the work of Spanish Artist Luis Urculo and students from the School of the Art Institute, … [Read more...] about Art on the Mart
Chicago Poetry Festival
Celebrate Poetry Month and all the notable literary stars that Chicago has birthed at the 27th annual Chicago Poetry Fest at the Harold Washington Library on April 27, 20226. Enjoy a day of free poetry events for all ages and backgrounds at this engaging event. Attend poetry workshops, listen … [Read more...] about Chicago Poetry Festival
View Cherry Blossoms in Chicago
The delicate blooms of cherry blossom trees are a beloved marker of the spring season but you don't have to travel to Japan to enjoy them. Chicago's cherry blossom season typically runs from late April to early May in Jackson Park. Head to Hyde Park and the Garden of the … [Read more...] about View Cherry Blossoms in Chicago
